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Diethylamine → tert-butyl N-[(3R)-3-[3-[4-(5-ethoxy-2-fluoro-phenyl)-6-methyl-pyrimidin-2-yl]prop-2-ynyl]-1-methyl-2-oxo-pyrrolidin-3-yl]carbamate

HRID 626899
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 626899
[CH3:1][N:2]1[CH2:6][CH2:5][C@:4]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])([CH2:7][C:8]#[CH:9])[C:3]1=[O:18].[CH2:19]([O:21][C:22]1[CH:23]=[CH:24][C:25]([F:36])=[C:26]([C:28]2[CH:33]=[C:32]([CH3:34])[N:31]=[C:30](I)[N:29]=2)[CH:27]=1)[CH3:20].N(CC)CC>C1COCC1.CCOC(C)=O.CCCC(C)C.[Cu](I)I>[CH2:19]([O:21][C:22]1[CH:23]=[CH:24][C:25]([F:36])=[C:26]([C:28]2[CH:33]=[C:32]([CH3:34])[N:31]=[C:30]([C:9]#[C:8][CH2:7][C@@:4]3([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:15])([CH3:14])[CH3:16])[CH2:5][CH2:6][N:2]([CH3:1])[C:3]3=[O:18])[N:29]=2)[CH:27]=1)[CH3:20]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 3

HCID 8021DiethylamineHCID 900151884-(5-Ethoxy-2-fluoro-phenyl)-2-iodo-6-methyl-pyrimidineHCID 90015672tert-Butyl N-[(3R)-1-methyl-2-oxo-3-prop-2-ynyl-pyrrolidin-3-yl]carbamate

Produkt 1

HCID 90015138tert-butyl N-[(3R)-3-[3-[4-(5-ethoxy-2-fluoro-phenyl)-6-methyl-pyrimidin-2-yl]prop-2-ynyl]-1-methyl-2-oxo-pyrrolidin-3-yl]carbamateAusbeute 90,9 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 83717Copper iodideKatalysator
HCID 8028TetrahydrofuranLösungsmittel
HCID 21882781Isohexane ethyl acetateLösungsmittel

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

Copper iodide (26.27 mg, 0.14 mmol), followed by PdCl2(Ph3P)2 (48.41 mg, 0.07 mmol) was added portionwise to a solution of the tert-butyl N-[(3R)-1-methyl-2-oxo-3-prop-2-ynyl-pyrrolidin-3-yl]carbamate (which may be prepared as described in Description 10) (348 mg, 1.38 mmol), 4-(5-ethoxy-2-fluoro-phenyl)-2-iodo-6-methyl-pyrimidine (which may be prepared as described in D17) (642.17 mg, 1.79 mmol) and Et2NH (0.71 mL, 6.9 mmol) in THF (10 mL) under N2 and the reaction was stirred at 20° C. for 18 hrs. The solvent was evaporated and the residue was dissolved in EtOAc and washed with water. The organic layer was dried (Na2SO4) and the solvent was evaporated to afford an oil. This was purified on a Biotage SP4 using a 25 g SNAP cartridge, eluting with 50 to 100% EtOAc/i-hexane affording the tert-butyl N-[(3R)-3-[3-[4-(5-ethoxy-2-fluoro-phenyl)-6-methyl-pyrimidin-2-yl]prop-2-ynyl]-1-methyl-2-oxo-pyrrolidin-3-yl]carbamate (D18) (605 mg, 1.2538 mmol, 90.9% yield) as a pale yellow foam.

Aufarbeitung

  1. customThe solvent was evaporated
  2. dissolutionthe residue was dissolved in EtOAc
  3. washwashed with water
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. customthe solvent was evaporated
  6. customto afford an oil
  7. customThis was purified on a Biotage

Quellen und Nachweise

ORD-Eintrag
ord-77f06b83645d4068a9e8dcc4dd6fdcc2
Quelldatensatz
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09309254B2

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